JP4253755B2 - アルミニウムアルキルアセトアセテート化合物及びその製法と印刷インキ付加剤としての使用 - Google Patents
アルミニウムアルキルアセトアセテート化合物及びその製法と印刷インキ付加剤としての使用 Download PDFInfo
- Publication number
- JP4253755B2 JP4253755B2 JP2000513825A JP2000513825A JP4253755B2 JP 4253755 B2 JP4253755 B2 JP 4253755B2 JP 2000513825 A JP2000513825 A JP 2000513825A JP 2000513825 A JP2000513825 A JP 2000513825A JP 4253755 B2 JP4253755 B2 JP 4253755B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- aluminum
- composition according
- compound
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 Aluminum alkyl acetoacetate compounds Chemical class 0.000 title claims description 35
- 229910052782 aluminium Inorganic materials 0.000 title claims description 29
- 238000007639 printing Methods 0.000 title claims description 23
- 239000000654 additive Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 33
- 239000000976 ink Substances 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 8
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- MQPPCKJJFDNPHJ-UHFFFAOYSA-K aluminum;3-oxohexanoate Chemical compound [Al+3].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O MQPPCKJJFDNPHJ-UHFFFAOYSA-K 0.000 claims description 2
- LSOLDYDKQUFGGM-UHFFFAOYSA-K aluminum;3-oxopentanoate Chemical compound [Al+3].CCC(=O)CC([O-])=O.CCC(=O)CC([O-])=O.CCC(=O)CC([O-])=O LSOLDYDKQUFGGM-UHFFFAOYSA-K 0.000 claims description 2
- 238000010894 electron beam technology Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 239000001023 inorganic pigment Substances 0.000 claims description 2
- 239000012860 organic pigment Substances 0.000 claims description 2
- 239000004584 polyacrylic acid Substances 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 7
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000013032 Hydrocarbon resin Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229920006270 hydrocarbon resin Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IKHOZNOYZQPPCK-UHFFFAOYSA-K aluminum;4,4-diethyl-3-oxohexanoate Chemical compound [Al+3].CCC(CC)(CC)C(=O)CC([O-])=O.CCC(CC)(CC)C(=O)CC([O-])=O.CCC(CC)(CC)C(=O)CC([O-])=O IKHOZNOYZQPPCK-UHFFFAOYSA-K 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical group C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- HLOLVQSTCUVLJD-UHFFFAOYSA-N ethyl 3-oxobutanoate 3-oxohexanoic acid Chemical compound CCCC(=O)CC(O)=O.CCOC(=O)CC(C)=O HLOLVQSTCUVLJD-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742828.2 | 1997-09-27 | ||
| DE19742828A DE19742828C1 (de) | 1997-09-27 | 1997-09-27 | Aluminiumalkylacetoacetat-Verbindungen, deren Herstellung und Verwendung als Druckfarbenadditive |
| PCT/DE1998/002860 WO1999016739A1 (de) | 1997-09-27 | 1998-09-25 | Aluminiumalkylacetoacetat-verbindungen, deren herstellung und verwendung als druckfarbenadditive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001518531A JP2001518531A (ja) | 2001-10-16 |
| JP4253755B2 true JP4253755B2 (ja) | 2009-04-15 |
Family
ID=7843909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000513825A Expired - Fee Related JP4253755B2 (ja) | 1997-09-27 | 1998-09-25 | アルミニウムアルキルアセトアセテート化合物及びその製法と印刷インキ付加剤としての使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6887398B1 (de) |
| EP (1) | EP1017665B1 (de) |
| JP (1) | JP4253755B2 (de) |
| AU (1) | AU1223699A (de) |
| DE (2) | DE19742828C1 (de) |
| HU (1) | HUP0202257A2 (de) |
| WO (1) | WO1999016739A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI303533B (en) * | 2001-06-15 | 2008-11-21 | Oled T Ltd | Electroluminescent devices |
| US7888521B2 (en) * | 2006-08-24 | 2011-02-15 | Chattem Chemicals, Inc. | Aluminum chelates |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE269142C (de) | ||||
| US2044968A (en) * | 1932-01-23 | 1936-06-23 | Resinous Prod & Chemical Co | Metal salts of oxyacedic acids |
| GB772144A (en) * | 1954-01-11 | 1957-04-10 | Hardman & Holden Ltd | Improvements relating to aluminium alcoholate derivatives |
| BE550505A (de) * | 1955-08-24 | |||
| US4264370A (en) * | 1976-03-01 | 1981-04-28 | Manchem Limited | Method for preparing aluminum-based air drying compositions |
| JPS5444909A (en) * | 1977-09-12 | 1979-04-09 | Mitsuboshi Inki Kk | Golden ink for printing |
| JPS6032661B2 (ja) * | 1980-01-16 | 1985-07-29 | 三菱瓦斯化学株式会社 | 一液性常温硬化型被覆組成物 |
| EP0065388B1 (de) * | 1981-05-08 | 1985-08-28 | Toray Industries, Inc. | Überzugsmittel |
| CA1296124C (en) * | 1986-11-06 | 1992-02-18 | Shinji Nakano | Paint resin |
| DD269142B1 (de) * | 1987-12-29 | 1992-07-02 | Forsch Rationalisierung Lacke | Verfahren zur herstellung eines gelbildners fuer druckfarben |
| US6159600A (en) * | 1997-02-14 | 2000-12-12 | Reliance Electric Technologies, Llc | Oxygen plasma resistant polymer for electrical devices |
| US5780525A (en) * | 1997-02-14 | 1998-07-14 | Reliance Electric Industrial Company | Photocurable composition for electrical insulation |
| US6051741A (en) * | 1997-10-17 | 2000-04-18 | Basf Aktiengesellschaft | Preparation of γ,δ-unsaturated ketones by the Carroll reaction, novel catalysts therefor and the preparation thereof |
-
1997
- 1997-09-27 DE DE19742828A patent/DE19742828C1/de not_active Expired - Fee Related
-
1998
- 1998-09-25 EP EP98955346A patent/EP1017665B1/de not_active Expired - Lifetime
- 1998-09-25 HU HU0202257A patent/HUP0202257A2/hu unknown
- 1998-09-25 DE DE59806879T patent/DE59806879D1/de not_active Expired - Lifetime
- 1998-09-25 JP JP2000513825A patent/JP4253755B2/ja not_active Expired - Fee Related
- 1998-09-25 WO PCT/DE1998/002860 patent/WO1999016739A1/de active IP Right Grant
- 1998-09-25 US US09/509,400 patent/US6887398B1/en not_active Expired - Fee Related
- 1998-09-25 AU AU12236/99A patent/AU1223699A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1017665A1 (de) | 2000-07-12 |
| DE19742828C1 (de) | 1999-05-12 |
| AU1223699A (en) | 1999-04-23 |
| US6887398B1 (en) | 2005-05-03 |
| EP1017665B1 (de) | 2003-01-08 |
| HUP0202257A2 (en) | 2002-10-28 |
| JP2001518531A (ja) | 2001-10-16 |
| WO1999016739A1 (de) | 1999-04-08 |
| DE59806879D1 (de) | 2003-02-13 |
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